title: Carotenoids with two chromophores: carotenoid retinoates.
abstract: In this study, carotenoid retinoates are described for the first time. The preparation was achieved by the azolide method. Various sec carotenols reacted with N-retinoylimidazol in the presence of catalytic amounts of sodium hydride. Mono- and diretinoates of (3R,3'R)-zeaxanthin and its (3S,3'S)-enantiomer, (9Z,9'Z; 3R,3'R)-alloxanthin, (3R,3'R)-7,8,7',8'-tetrahydro-3,3'-dihydroxy-β,β-carotene-8,8'-dione and (3R,6R,3'R,6'R)-ε,ε-carotene-3,3'-diol (lactucaxanthin), as well as monoretinoates of (3R,3'RS,6'R)-3'-methoxy-β,ε-caroten-3-ol, (3R,3'RS,6'R)-3-methoxy-β,ε-caroten-3'-ol, (2R,6'RS)-β,ε-caroten-2-ol, (3R,3'S; meso)-astaxanthin and (2'R)-aleuriaxanthin are reported in this study. Spectroscopic properties ((1)H-NMR mass spectrometry, visible and circular dichroism spectra) are discussed. Studies on other carotenoid derivatives with two chromophores are referred to here.
authors.affiliation: Department of Chemistry, Norwegian University of Science and Technology (NTNU), NO-7491, Trondheim, Norway.
authors.forename: Sissel
authors.initials: S
authors.lastname: Hertzberg
authors.forename: Bjart Frode
authors.initials: BF
authors.lastname: Lutnaes
authors.forename: Synnøve
authors.initials: S
authors.lastname: Liaaen-Jensen
mesh_terms: D000975:Antioxidants / Q000737:chemistry; D002338:Carotenoids / Q000737:chemistry*; D002942:Circular Dichroism; D004024:Dicyclohexylcarbodiimide; D004951:Esterification; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D017670:Sodium Compounds; D014212:Tretinoin / Q000737:chemistry*
chemical_list: D000975:Antioxidants; D017670:Sodium Compounds; C524957:sodium hydride; D002338:Carotenoids; D004024:Dicyclohexylcarbodiimide; D014212:Tretinoin